N-((2S,3S)-3-trans-ethoxycarbonyloxiran-2-carbonyl)-L-phenylalanine benzyl ester

Base Information

• Chemical Name: N-((2S,3S)-3-trans-ethoxycarbonyloxiran-2-carbonyl)-L-phenylalanine benzyl ester
• CAS No.: 128301-64-4
• Molecular Formula: C₂₂H₂₃NO₆
• Molecular Weight: 397.428
• Mol file: 128301-64-4.mol

Synonyms:N-((2S,3S)-3-trans-ethoxycarbonyloxiran-2-carbonyl)-L-phenylalanine benzyl ester

Chemical Property of N-((2S,3S)-3-trans-ethoxycarbonyloxiran-2-carbonyl)-L-phenylalanine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((2S,3S)-3-trans-ethoxycarbonyloxiran-2-carbonyl)-L-phenylalanine benzyl ester

There total 3 articles about N-((2S,3S)-3-trans-ethoxycarbonyloxiran-2-carbonyl)-L-phenylalanine benzyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

L-phenylalanine benzyl ester p-toluene-sulfonic acid salt (1738-78-9) + ethyl (2S,3S)-2,3-epoxysuccinate (63734-73-6,66647-16-3,68521-71-1,89886-73-7,93061-20-2,149884-11-7) → N-((2S,3S)-3-trans-ethoxycarbonyloxiran-2-carbonyl)-L-phenylalanine benzyl ester (128301-64-4)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In chloroform; at 0 - 23 ℃;

DOI:10.1055/s-1999-3648

Reference yield:

(2S,3S)-diethyl oxirane-2,3-dicarboxylate (3291-46-1,3291-47-2,61937-48-2,66647-17-4,74243-85-9,73890-18-3) → N-((2S,3S)-3-trans-ethoxycarbonyloxiran-2-carbonyl)-L-phenylalanine benzyl ester (128301-64-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 57.7 percent / 0.1M aq. KH₂PO₄, 1M aq. NaOH / 20 °C / pig liver esterase

2: 1.) DCC, 2.) HOBt / 1.) THF, 0.5 h, 2.) THF, a) -5 deg C, 1 h, b) 25 deg C, 2 d

With sodium hydroxide; potassium dihydrogenphosphate; benzotriazol-1-ol; dicyclohexyl-carbodiimide;

DOI:10.1006/bioo.1994.1017

Reference yield:

L-Phenylalanine benzyl ester (962-39-0) + ethyl (2S,3S)-2,3-epoxysuccinate (63734-73-6,66647-16-3,68521-71-1,89886-73-7,93061-20-2,149884-11-7) → N-((2S,3S)-3-trans-ethoxycarbonyloxiran-2-carbonyl)-L-phenylalanine benzyl ester (128301-64-4)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; Yield given. Multistep reaction; 1.) THF, 0.5 h, 2.) THF, a) -5 deg C, 1 h, b) 25 deg C, 2 d;

DOI:10.1006/bioo.1994.1017

upstream raw materials:

L-Phenylalanine benzyl ester

ethyl (2S,3S)-2,3-epoxysuccinate

L-phenylalanine benzyl ester p-toluene-sulfonic acid salt

(2S,3S)-diethyl oxirane-2,3-dicarboxylate

Downstream raw materials:

N-((2S,3S)-3-trans-ethoxycarbonyloxiran-2-carbonyl)-L-phenylalanine